Samyr Laine and his wife, Ayanna Alexander-Laine, started Freedom Trail Capital in 2023 and are looking to raise $50 million.
Both are former Olympians competing for Haiti and Trinidad and Tobago, respectively, in the triple jump. Now they put grit and determination to work for founders looking to launch and scale consumer brands.
“I love people and connecting with people,” Alexander-Laine told TechCrunch. “We know how to combine talent and business, and find that athletes are good in that space. We also have the stamina to conquer other things and other entities outside of sports.
He, along with his third general partner, Ivan Lopez, has invested in seven startups so far close to their first funding. These include a hair care company by Issa Rae called Sienna Naturals; a pet product company started by Kaley Cuoco called Oh Norman!; Ciara’s Ten to One Rum; and Kudos, a diaper company backed by Mark Cuban and Gwyneth Paltrow.
There are seven more investments in the pipeline as Freedom Trail Capital continues to raise capital, Laine told TechCrunch.
For the Olympics and beyond
Laine knows how to start and scale a company. He previously worked as senior vice president of operations and strategy at Westbrook, a venture firm founded by Will Smith and Jada Pinkett Smith. He also spent time as director of operations at Roc Nation, working with Jay-Z. Meanwhile, Alexander-Laine is pursuing a doctorate in business administration and will focus on health finance and health disparities.
Laine also knows what it’s like to fail. He tried out for the track team in seventh grade and ended up getting cut the following year. It wasn’t until middle school that he decided to try track again, this time seriously with the triple jump.
All this is good, though. Laine ended up going to Harvard and set several track records with the team. He is also roommate with Mark Zuckerberg. They had a four-person dorm room freshman year, and they shared bunk beds. Laine may have been the 11th person to log on to Facebook and try it, he said. He also fielded a trivia question on the show “Cash Cab” about the Olympian who was Zuckerberg’s roommate, Laine said.
“Mark has always been a craftsman, and we knew he was going to do amazing things,” Laine said.
When Laine transferred to the University of Texas, she was exposed to a whole new world of track and field. My friends there compete at a different level, because many of them are already world junior champions. Laine participated in his first Pan-American Games in 2007. He also tried out for the Olympics in 2008 and missed competing in the triple jump by several centimeters.
He balanced training and law school at Georgetown University while trying again for the Olympics in 2012 and qualifying. Many people tell me that this is too much, but now when someone asks for advice, he says, “Go for what you can’t do.”
“I thought if I could go to law school and balance it, I could get there,” said Laine. “At that time, I was number 7 in the world in the triple jump, and going to the London games, my goal was to win Haiti’s first medal since 1928. I qualified for the final but did not get a medal. .”
For 10 years, Laine and Alexander-Laine competed around the world as professionals in track and field. Laine learned from his friends at UT how to make money. They can also get sponsorship and financial assistance from the international Olympic committee.
Worked for Will Smith and Jay-Z
After that, he had several additional careers in sports before getting into entertainment and building his brand at Roc Nation. Laine worked with Jay-Z to build and scale a brand that included spirits, apparel, cannabis and book publishing divisions. He even managed several platinum recording artists. From there, he went to Westbrook to do the same for Smith and Pinkett Smith. He was there for four years before starting Freedom Trail Capital.
“I was not necessarily allocating capital and investing, but I have a front-line view into some of the investment decisions that the Roc Nation fund made,” Laine said. “I’m an operator at heart, so that gives me a unique perspective on how we’re diligent about investment opportunities and can support our portfolio companies.”
Freedom Trail Capital’s thesis is to invest in talent-led businesses, and they know what they’re looking for. Laine has helped Smith and Jay-Z become successful with several brands, but has also seen several cases where talent-led brands don’t go as expected.
Now that he’s on the other side as an investor, Laine says his job is to produce and insure entrepreneurs as well as protect their limited partners from bad investments.
“Having been in a place where I know what it takes to win the brand, we look at our portfolio very differently than most people,” Laine said.
Not every product has what it takes, he said. Freedom Trail Capital is looking for product-market fit, of course. If there is a celebrity behind it, there should be a good relationship between the person and the product, and the person should roll up his sleeves and get to work.
Laine said there have been times when she’s encountered celebrities who refuse to take photos or go to Target to promote their products.
“We’re not just talking about endorsements anymore,” Laine said. “We’re talking about you owning an important part of this company. I’ve seen things fall by the wayside, and promising brands and companies fail.
